A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition

被引:36
作者
Gangaprasad, D. [1 ]
Raj, J. Paul [1 ]
Kiranmye, T. [1 ]
Sasikala, R. [1 ]
Karthikeyan, K. [1 ]
Rani, S. Kutti [1 ]
Elangovan, J. [2 ]
机构
[1] BS Abdur Rahman Univ, Dept Chem, Seethakathi Estate, Madras 600048, Tamil Nadu, India
[2] HH Rajahs Coll, Dept Chem, Pudukkottai 622001, Tamil Nadu, India
关键词
3+2] cycloaddition; Azide-olefin; CuO nanoparticles; Solvent-free condition; Catalyst recyclability; CLICK CHEMISTRY; REGIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; BRONSTED ACID; TRIAZOLE; ALKYNES; TRANSANNULATION; CONSTRUCTION; LIGATION;
D O I
10.1016/j.tetlet.2016.06.004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nanoparticle catalyst is described. In the presence of the catalyst under solvent-free condition, nitro group is retained in the product while it gets eliminated in the absence of the catalyst. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3105 / 3108
页数:4
相关论文
共 64 条
[51]   Click Chemistry for Drug Development and Diverse Chemical-Biology Applications [J].
Thirumurugan, Prakasam ;
Matosiuk, Dariusz ;
Jozwiak, Krzysztof .
CHEMICAL REVIEWS, 2013, 113 (07) :4905-4979
[52]   A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles [J].
Thomas, Joice ;
John, Jubi ;
Parekh, Nikita ;
Dehaen, Wim .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) :10155-10159
[53]   Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides [J].
Tornoe, CW ;
Christensen, C ;
Meldal, M .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3057-3064
[54]   Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes [J].
Tron, Gian Cesare ;
Pirali, Tracey ;
Billington, Ricbard A. ;
Canonico, Pier Luigi ;
Sorba, Giovanni ;
Genazzani, Armando A. .
MEDICINAL RESEARCH REVIEWS, 2008, 28 (02) :278-308
[55]   Oxidative Palladium Catalysis in SNAr Reactions Leading to Heteroaryl Ethers from Pyridotriazol-1-yloxy Heterocycles with Aryl Boronic Acids [J].
Wacharasindhu, Sumrit ;
Bardhan, Sujata ;
Wan, Zhao-Kui ;
Tabei, Keiko ;
Mansour, Tarek S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (12) :4174-+
[56]   Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles [J].
Wang, Lei ;
Peng, Shiyong ;
Danence, Lee Jin Tu ;
Gao, Yaojun ;
Wang, Jian .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) :6088-6093
[57]   Ce(OTf)3-Catalyzed [3+2] Cycloaddition of Azides with Nitroolefins: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles [J].
Wang, Ying-Chun ;
Xie, Yu-Yang ;
Qu, Hong-En ;
Wang, Heng-Shan ;
Pan, Ying-Ming ;
Huang, Fu-Ping .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) :4463-4469
[58]   Regioselective Synthesis of β-Aryl Enaminones and 1,4,5-Trisubstituted 1,2,3-Triazoles from Chalcones and Benzyl Azides [J].
Xie, Yu-Yang ;
Wang, Ying-Chun ;
Qu, Hong-En ;
Tan, Xian-Chun ;
Wang, Heng-Shan ;
Pan, Ying-Ming .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) :3347-3355
[59]   Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent [J].
Yeung, Dwun Kit Jonathan ;
Gao, Tao ;
Huang, Jiayao ;
Sun, Shaofa ;
Guo, Haibing ;
Wang, Jian .
GREEN CHEMISTRY, 2013, 15 (09) :2384-2388
[60]  
Zefirov N.S., 1971, Chem. Commoun, P1001